I can be pleasant just as much as she is in our daily interactions, but at what point in how do I start attempting at reconnecting?
The short answer is.....when she stops being a WW.
What images do you have, when you think of reconnecting? I believe it was your thread where I said that the WW does not give the bomb drop in order to wake up her H. She is not wanting him to start working on their MR. She wants to be free. The IHS is simply a step in that direction, as far as she is concerned.
I'm not sure you can reconnect with a WW. It would be very unhealthy for you, IMHO. At the very best, she would friend zone you. Instead of thinking at what point you can start reconnecting, you first need to let her go. Can you do it?
It is not about what you feel should work in your M. It is about doing the work that gets the right results. Do what works!